title: Synthesis and biological activity of phosphoglycolipids from Thermus thermophilus.
abstract: An extreme thermophile, Thermus thermophilus, has very unique glycolipids on the cell surface. The acidic immunostimulatory phosphoglycolipid of T. thermophilus was synthesized for the first time, with newly developed glycosylation methods using 3-nitropyridyl (3NPy) and 4,6-dimethoxy-1,3,5-triazin-2-yl (DMT) glycosides as glycosyl donors. The analogues of the phosphoglycolipid, which include a diastereomer possessing the opposite configuration at the diacyl glycerol moiety, were also synthesized. The biological activities of the synthesized compounds were elucidated with cytokine inductions (IL-6 and TNF-α). A synthetic phosphoglycolipid with a natural-type diacyl glycerol configuration showed apparent immunostimulatory activity, whereas its diastereomer did not. The present study revealed that the configuration at the diacyl glycerol moiety of the phosphoglycolipids is important for immunostimulation, suggesting the existence of the particular receptor/recognizing protein that can recognize the stereochemistry of the glycerol part.
authors.affiliation: Department of Chemistry, Graduate School of Science, Osaka University, Toyonaka, Osaka 560-0043, Japan. yukarif@chem.sci.osaka-u.ac.jp
authors.forename: Yukari
authors.initials: Y
authors.lastname: Fujimoto
authors.forename: Kunihiro
authors.initials: K
authors.lastname: Mitsunobe
authors.forename: Satoko
authors.initials: S
authors.lastname: Fujiwara
authors.forename: Motoko
authors.initials: M
authors.lastname: Mori
authors.forename: Masahiro
authors.initials: M
authors.lastname: Hashimoto
authors.forename: Yasuo
authors.initials: Y
authors.lastname: Suda
authors.forename: Shoichi
authors.initials: S
authors.lastname: Kusumoto
authors.forename: Koichi
authors.initials: K
authors.lastname: Fukase
mesh_terms: D004305:Dose-Response Relationship, Drug; D006017:Glycolipids / Q000138:chemical synthesis* / Q000302:isolation & purification / Q000494:pharmacology*; D006801:Humans; D015850:Interleukin-6 / Q000096:biosynthesis / Q000097:blood / Q000276:immunology; D015394:Molecular Structure; D016963:Thermus thermophilus / Q000737:chemistry*; D014409:Tumor Necrosis Factor-alpha / Q000096:biosynthesis / Q000097:blood / Q000276:immunology
chemical_list: D006017:Glycolipids; D015850:Interleukin-6; D014409:Tumor Necrosis Factor-alpha